Regio- and stereospecific synthesis of (O-tips)-protected 2- hydroxyalkylmercaptans from epoxides and triisopropylsilanethiol

Article abstract of DOI:10.1016/S0040-4039(98)00834-X

The regiospecific ring-opening of both mono- and disubstituted epoxides with triisopropylsilanethiol/DBU has been developed to provide 2- triisopropylsilylaxyalkylthiols (1) in high yields. Non-racemic 1 is easily prepared from optically active epoxides. Moreover, the further elaboration of 1, through the exposed mercapto functionality, provides controlled access to unsymmetrical mono-protected bis-(2-hydroxyalkyl) sulfides and functionalized thioesters.